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Table 3 Second-order reaction rate constant between unstrained olefin dienophiles with Fluorescein-Tetrazine

From: Tetrazine ligation for chemical proteomics

Entry

Unstrained Olefin

k (10−3 M−2 s−1)

1

prop-2-en-1-ol

9.4 ± 1.2

2

(E)-but-2-en-1-ol

1.9 ± 0.1

3

but-3-en-1-ol

26 ± 5

4

pent-4-en-1-ol

36 ± 4

5

2-(vinyloxy) ethan-1-ol

81 ± 1

6

(R)-N-(5-aminohexyl) acrylamide

1.2 ± 0.1

7

(R)-N-(5-aminohexyl) but-3-enamide

1.7 ± 0.2

8

(R)-N-(5-aminohexyl) pent-4-enamide

11 ± 2

9

(R)-N-(5-aminohexyl) hex-5-enamide

16 ± 1

10

(R,E)-N-(5-aminohexyl)-3-methoxyacrylamide

19 ± 1

  1. Fluorescein-Tetrazine = N-(2-(3-(3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthen]-5-yl) thioureido) ethyl)-4-(1,2,4,5-tetrazin-3-yl) benzamide